So a few things GMs aren't really in charge of Guilds anymore, GMs tackle things in groups largely.
As far as 'eventy' things the Thieves' Guild is fairly lone wolf and isolated from each other, and maybe that's a good thing because how does one weed something that doesn't have much of any kind of root, and a system that isn't interconnected.
My suggestion is if you have passion and time, and decent imagination run with something, here is one of the irksome parts of being a Thief, so we're supposed to be all stealthy and covert right, ya well you kinda NEED to get noticed often and continuously to push an event (at least that's my take on that). So might kinda feel like your running against the grain of what a Thief should be doing.
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"I think anything that forces you to do something no sane adventurer would do just in order to train is ridiculous."
DR-SOCHARIS
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"Phelim, what have I wrought?"
GM NaOHHI
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Victory Over Lyras, on the 397th year and 156 S.V.o.L.t.R
